Water → 3-(3-Cyano-4-methoxy-5-trifluoromethylbenzoyl)-5-trifluoromethyl-2,3-dihydro-1,3-benzothiazole

HRID 385159Notes

Reaction equation

HRID 385159 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[CH:5][C:6]2[S:10][CH2:9][NH:8][C:7]=2[CH:11]=1.C(N(CC)CC)C.[C:21]([C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([C:34]([F:37])([F:36])[F:35])[C:31]=1[O:32][CH3:33])[C:26](Cl)=[O:27])#[N:22].O>ClCCl>[C:21]([C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([C:34]([F:35])([F:37])[F:36])[C:31]=1[O:32][CH3:33])[C:26]([N:8]1[C:7]2[CH:11]=[C:3]([C:2]([F:1])([F:12])[F:13])[CH:4]=[CH:5][C:6]=2[S:10][CH2:9]1)=[O:27])#[N:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 218361675-Trifluoromethyl-2,3-dihydro-1,3-benzothiazoleHCID 866681503-Cyano-4-methoxy-5-trifluoromethylbenzoylchloride

Product 1

HCID 866681853-(3-Cyano-4-methoxy-5-trifluoromethylbenzoyl)-5-trifluoromethyl-2,3-dihydro-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-trifluoromethyl-2,3-dihydro-1,3-benzothiazole was dissolved in dichloromethane (5 mL), and triethylamine (0.56 mL) and 3-cyano-4-methoxy-5-trifluoromethylbenzoyl chloride (839 mg) were added to the solution, and then the mixture was stirred at room temperature for 1.5 hours. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1) to obtain the title compound (479 mg) as a pale yellow amorphous product.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-ab18ed94e23845379868f33a23005a84
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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